US3336324A - N-allyl-pyridine-3-sulfonic acid betaine - Google Patents
N-allyl-pyridine-3-sulfonic acid betaine Download PDFInfo
- Publication number
- US3336324A US3336324A US560077A US56007766A US3336324A US 3336324 A US3336324 A US 3336324A US 560077 A US560077 A US 560077A US 56007766 A US56007766 A US 56007766A US 3336324 A US3336324 A US 3336324A
- Authority
- US
- United States
- Prior art keywords
- pyridine
- sulfonic acid
- allyl
- acid betaine
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/12—Electroplating: Baths therefor from solutions of nickel or cobalt
- C25D3/14—Electroplating: Baths therefor from solutions of nickel or cobalt from baths containing acetylenic or heterocyclic compounds
- C25D3/18—Heterocyclic compounds
Definitions
- Cilag-Chemie a corporation of Switzerland N0 Drawing. Filed June 24, 1966, Ser. No. 560,077 1 Claim. (Cl. 260294.8)
- This invention relates to a new organic chemical compound, and, more particularly, to N-allyl-pyridine-3- sulfonic acid betaine and the preparation thereof.
- This compound may be structurally represented by the following formula:
- an aqueous acidic solution of a nickel salt is generally employed, which solution generally contains a luster-promoting agent. It has been found that lustrous and levelled nickel coatings are obtained when the subject compound, N- allyl-pyridine-S-sulfonic acid betaine, is used as an additive in conventional galvanic nickel baths. In addition to promoting luster, this additive has the property of levelling the rough and uneven surface of metals.
- the subject compound may be prepared by interacting 3-pyridine sulfonic acid with allyl chloride in the presence of a base such as, for example, sodium hydroxide.
- Example I To a solution of 30.4 g. sodium hydroxide in 120 ml. water, 120 g. 3-pyridine sulfonic acid are added with 190 g. ethanol and 57.6 g. allylchloride. This mixture is stirred for 3 hours at 105 C. in a stainless steel autoclave. After allowing to cool, 100 ml. Water is added and the whole 3,336,324 Patented Aug. 15, 1967 solution is boiled with charcoal for about 10 minutes,
- Example II This example illustrates a typical galvanic nickel bath employing the subject compound:
Description
United States Patent 3,336,324 N-ALLYL-PYRIDINE-S-SULFONIC ACID BETAINE Carl Richter and Georg Feth, Schalfhausen, Switzerland,
assignors to Cilag-Chemie, a corporation of Switzerland N0 Drawing. Filed June 24, 1966, Ser. No. 560,077 1 Claim. (Cl. 260294.8)
This invention relates to a new organic chemical compound, and, more particularly, to N-allyl-pyridine-3- sulfonic acid betaine and the preparation thereof. This compound may be structurally represented by the following formula:
For the electrodeposition of nickel coatings, an aqueous acidic solution of a nickel salt is generally employed, which solution generally contains a luster-promoting agent. It has been found that lustrous and levelled nickel coatings are obtained when the subject compound, N- allyl-pyridine-S-sulfonic acid betaine, is used as an additive in conventional galvanic nickel baths. In addition to promoting luster, this additive has the property of levelling the rough and uneven surface of metals.
The subject compound may be prepared by interacting 3-pyridine sulfonic acid with allyl chloride in the presence of a base such as, for example, sodium hydroxide.
The following examples are intended to illustrate, but not to limit, the scope of the present invention.
Example I To a solution of 30.4 g. sodium hydroxide in 120 ml. water, 120 g. 3-pyridine sulfonic acid are added with 190 g. ethanol and 57.6 g. allylchloride. This mixture is stirred for 3 hours at 105 C. in a stainless steel autoclave. After allowing to cool, 100 ml. Water is added and the whole 3,336,324 Patented Aug. 15, 1967 solution is boiled with charcoal for about 10 minutes,
followed by filtration. The clear solution is evaporated to dryness in vacuo. The residue is treated with 185 g.
of methanol and ml. Water, then heated to reflux and 5 filtered. The residue is now Washed with 20 g. methanol.
The filtrate is cooled to 5 C. and allowed to stand overnight. Then the precipitate is separated by filtration and washed with 120 g. methanol. After drying at 70 C. in vacuo, N-allyl-pyridine-3-sulfonic acid betaine is obtained; M.P. 172176 C.
Example II This example illustrates a typical galvanic nickel bath employing the subject compound:
What is claimed is: N-allyl-pyridine-S-sulfonic acid betaine.
No references cited.
WALTER A. MODANCE, Primary Examiner.
ALAN L. ROTMAN, Asssistanl Examiner.
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US560107A US3444056A (en) | 1966-06-24 | 1966-06-24 | Nickel electroplating electrolyte |
US560077A US3336324A (en) | 1966-06-24 | 1966-06-24 | N-allyl-pyridine-3-sulfonic acid betaine |
GB35608/66A GB1128519A (en) | 1966-06-24 | 1966-08-09 | Improvements in or relating to the electro-deposition of nickel |
DE19661670376 DE1670376A1 (en) | 1966-06-24 | 1966-08-16 | Electrolytic nickel bath |
CH1187066A CH484282A (en) | 1966-06-24 | 1966-08-17 | Electrolytic nickel bath |
FR79343A FR1496339A (en) | 1966-06-24 | 1966-10-10 | Bath for the electroplating of plain and shiny nickel and its preparation process |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US56010766A | 1966-06-24 | 1966-06-24 | |
US560077A US3336324A (en) | 1966-06-24 | 1966-06-24 | N-allyl-pyridine-3-sulfonic acid betaine |
Publications (1)
Publication Number | Publication Date |
---|---|
US3336324A true US3336324A (en) | 1967-08-15 |
Family
ID=27072242
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US560077A Expired - Lifetime US3336324A (en) | 1966-06-24 | 1966-06-24 | N-allyl-pyridine-3-sulfonic acid betaine |
US560107A Expired - Lifetime US3444056A (en) | 1966-06-24 | 1966-06-24 | Nickel electroplating electrolyte |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US560107A Expired - Lifetime US3444056A (en) | 1966-06-24 | 1966-06-24 | Nickel electroplating electrolyte |
Country Status (5)
Country | Link |
---|---|
US (2) | US3336324A (en) |
CH (1) | CH484282A (en) |
DE (1) | DE1670376A1 (en) |
FR (1) | FR1496339A (en) |
GB (1) | GB1128519A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3444056A (en) * | 1966-06-24 | 1969-05-13 | Cilag Chemie | Nickel electroplating electrolyte |
US4120859A (en) * | 1977-01-27 | 1978-10-17 | Cilag-Chemie A.G. | (N-Substituted-pyridyl)-alkyl sulfonic acid betaines as electroplating additives |
US9594063B2 (en) | 2012-03-16 | 2017-03-14 | National Research Council Of Canada | Retention index standards for liquid chromatography |
US9752244B2 (en) | 2013-05-08 | 2017-09-05 | Atotech Deutschland Gmbh | Galvanic nickel electroplating bath for depositing a semi-bright nickel |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4067785A (en) * | 1976-03-12 | 1978-01-10 | Cilag-Chemie A.G. | Electroplating additives |
GB1578168A (en) * | 1976-03-12 | 1980-11-05 | Cilag Chemie | Pyridyl alkylsulphonic acid derivatives and their use in electroplating baths |
US4148797A (en) * | 1977-07-15 | 1979-04-10 | Cilag-Chemie A.G. | (N-Substituted pyridyl)-alkyl sulfonic acid betaines as electroplating additives |
US4894123A (en) * | 1988-11-01 | 1990-01-16 | Helmich Arthur R | High efficiency water distiller |
JP6024714B2 (en) * | 2013-10-03 | 2016-11-16 | トヨタ自動車株式会社 | Nickel solution for film formation and film forming method using the same |
KR20210146520A (en) * | 2020-05-27 | 2021-12-06 | 주식회사 엘지에너지솔루션 | Electrolyte additives for secondary battery, non-aqueous electrolyte for secondary battery comprising the same and secondary battery |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL100419C (en) * | 1955-03-16 | |||
US3006822A (en) * | 1957-05-08 | 1961-10-31 | Langbein Pfanhauser Werke Ag | Electro-deposition of nickel coatings |
DE1238032B (en) * | 1962-07-21 | 1967-04-06 | Dehydag Gmbh | Process for the preparation of sulfobetaines containing oxy groups |
DE1191652B (en) * | 1963-05-15 | 1965-04-22 | Dehydag Gmbh | Acid galvanic nickel bath |
US3336324A (en) * | 1966-06-24 | 1967-08-15 | Cilag Chemie | N-allyl-pyridine-3-sulfonic acid betaine |
-
1966
- 1966-06-24 US US560077A patent/US3336324A/en not_active Expired - Lifetime
- 1966-06-24 US US560107A patent/US3444056A/en not_active Expired - Lifetime
- 1966-08-09 GB GB35608/66A patent/GB1128519A/en not_active Expired
- 1966-08-16 DE DE19661670376 patent/DE1670376A1/en active Pending
- 1966-08-17 CH CH1187066A patent/CH484282A/en not_active IP Right Cessation
- 1966-10-10 FR FR79343A patent/FR1496339A/en not_active Expired
Non-Patent Citations (1)
Title |
---|
None * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3444056A (en) * | 1966-06-24 | 1969-05-13 | Cilag Chemie | Nickel electroplating electrolyte |
US4120859A (en) * | 1977-01-27 | 1978-10-17 | Cilag-Chemie A.G. | (N-Substituted-pyridyl)-alkyl sulfonic acid betaines as electroplating additives |
US9594063B2 (en) | 2012-03-16 | 2017-03-14 | National Research Council Of Canada | Retention index standards for liquid chromatography |
US9752244B2 (en) | 2013-05-08 | 2017-09-05 | Atotech Deutschland Gmbh | Galvanic nickel electroplating bath for depositing a semi-bright nickel |
US9790607B1 (en) | 2013-05-08 | 2017-10-17 | Atotech Deutschland Gmbh | 3-(carbamoyl) pyridinium-1-YL-propane-1-sulfonates useful in electroplating baths |
Also Published As
Publication number | Publication date |
---|---|
FR1496339A (en) | 1967-09-29 |
DE1670376A1 (en) | 1971-01-14 |
US3444056A (en) | 1969-05-13 |
GB1128519A (en) | 1968-09-25 |
CH484282A (en) | 1970-01-15 |
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